CA2203184A1 - Sun-protection preparation with increased light-protection factor - Google Patents
Sun-protection preparation with increased light-protection factorInfo
- Publication number
- CA2203184A1 CA2203184A1 CA002203184A CA2203184A CA2203184A1 CA 2203184 A1 CA2203184 A1 CA 2203184A1 CA 002203184 A CA002203184 A CA 002203184A CA 2203184 A CA2203184 A CA 2203184A CA 2203184 A1 CA2203184 A1 CA 2203184A1
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- Canada
- Prior art keywords
- sun protection
- sun
- preparation according
- protection preparation
- ranges
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Lighting Device Outwards From Vehicle And Optical Signal (AREA)
- Prostheses (AREA)
- Led Device Packages (AREA)
Abstract
The invention concerns a sun-protection preparation with an increased lightprotection factor, consisting of (A) a fine-particle, crosslinked poly(methylsiloxane) with a particle size ranging from 1 to 10 .mu.m, the poly(methylsiloxane) having given further parameters, (B) octyldodecylneopentanoate, (C) formulation aids, and (D) additives. The ratio of (A) to (B) ranges from 1 : 2 to 10, and the portion of (A) and (B) ranges from 3 to 12 wt %, relative to the total composition.
Description
05~01~7 0~: 12 FAX 613 230 8842 ~r~lTT C 6VT T'M 1~ 002~013 W0 9~/15772 PCT/DE95/01701 Sun p~otection p~eparation with an increased sun protecti~n facto~
lU This invention relates to a sun prote~tion preparation with an inc~eased sun p~otection factor.
Numerous sun protection prepara~ions have become known.
~opic~l sun p~otection prepa~ations, as a rule, can either be catego~ized as chemical or physical sun p~otection p~ep-a~ations. The chemical sun protection p~eparations th~t are of interest here contain one or seve~al W-abso~bi~g sub-s~ances and, after a thin and invisible film of such prep-aration ha~ been applied to the skin, act as a screen p~e-venting ultraviolet radiation f~om penetrating to the living zU cells of the epidermis. Chemical sun protection prepa~ations are usu~lly colourless a-~ they do not contain any su~stances that absor~ ~isible llght, and they a~e therefo~e cosmetically acceptable for most people provided tha~ they do not irritate the eye~, are non-photo~ensitizing, stable and non-volatile, and that they d~ no~ leave any s~ains on people'~ skin and clothing. Most commercial sun protection p~eparations contain one or seve~l chemicals which absorb W-9 ~diation, and furthermore they contain a moistu~izing base. A more recent ingredient of known sun prote~tion p~ep-arations ha~e been W-A radiation-abso~bing substan~e~, ~ostly variou~ benzophenones. Most chemical sun protection prepa~ations used comp~ise p-aminobenzoic acid (PABA), PABA
esters (amyl dimethyl PA~A and octyl dimethyl PABA), ~enzo-pheno~es, cinnamates (octyl methoxy~innamate and cinnoxate~, salicylates (homomenthyl salicylate), and anthranilates.
Sun protec~ion prepara~ions that ~on~ain a-hydroxy acids or their de~ivatives have been known from W0 94/06409 05~01~a7 0~:12 FAX ~13 230 884~cA 02203l84 1997-04~ oo3~ol3 ~ (PCT/USg2~11037) by Perricone et al. Fu~thermore, ~un pro-tec~ion preparations have been known from ~093/~g729 (PCT/US93/02712) that contain a combination of retinoic acid and vario~s deri~atives thereof with pharm~e~ticals.
W093/11742 (PCT/EP~2/02H97) p~oposes a po~tion of 0.5 to 30 wt % of titanium dioxide and/o~ zinc oxide, or ~.001 to 2 wt % of iron oxide, the mean prim~y particle size of said iron oxide being about 2~0 nm. These pa~ticles may also be ~oated with phospholipids.
It has become a generally accepted practi~e to specify the sun protection factor ~SP~) o~ ~un protection prep~a-tions. There is a great inte~est in increasin~ ~aid sun p~otection facto~ so that the product can be used by many people and in~ariably ca~ses a pleasant dermal se~sation.
The medl~m-~ange sun p~otection ~acto~s from SFP l~ to 20 are of pa~ticula~ interest in this respect.
It is the~efore the ob3ect of the invention ~o provide novel sun protection preparations having an improved ~un p~otection faotor.
lU This invention relates to a sun prote~tion preparation with an inc~eased sun p~otection factor.
Numerous sun protection prepara~ions have become known.
~opic~l sun p~otection prepa~ations, as a rule, can either be catego~ized as chemical or physical sun p~otection p~ep-a~ations. The chemical sun protection p~eparations th~t are of interest here contain one or seve~al W-abso~bi~g sub-s~ances and, after a thin and invisible film of such prep-aration ha~ been applied to the skin, act as a screen p~e-venting ultraviolet radiation f~om penetrating to the living zU cells of the epidermis. Chemical sun protection prepa~ations are usu~lly colourless a-~ they do not contain any su~stances that absor~ ~isible llght, and they a~e therefo~e cosmetically acceptable for most people provided tha~ they do not irritate the eye~, are non-photo~ensitizing, stable and non-volatile, and that they d~ no~ leave any s~ains on people'~ skin and clothing. Most commercial sun protection p~eparations contain one or seve~l chemicals which absorb W-9 ~diation, and furthermore they contain a moistu~izing base. A more recent ingredient of known sun prote~tion p~ep-arations ha~e been W-A radiation-abso~bing substan~e~, ~ostly variou~ benzophenones. Most chemical sun protection prepa~ations used comp~ise p-aminobenzoic acid (PABA), PABA
esters (amyl dimethyl PA~A and octyl dimethyl PABA), ~enzo-pheno~es, cinnamates (octyl methoxy~innamate and cinnoxate~, salicylates (homomenthyl salicylate), and anthranilates.
Sun protec~ion prepara~ions that ~on~ain a-hydroxy acids or their de~ivatives have been known from W0 94/06409 05~01~a7 0~:12 FAX ~13 230 884~cA 02203l84 1997-04~ oo3~ol3 ~ (PCT/USg2~11037) by Perricone et al. Fu~thermore, ~un pro-tec~ion preparations have been known from ~093/~g729 (PCT/US93/02712) that contain a combination of retinoic acid and vario~s deri~atives thereof with pharm~e~ticals.
W093/11742 (PCT/EP~2/02H97) p~oposes a po~tion of 0.5 to 30 wt % of titanium dioxide and/o~ zinc oxide, or ~.001 to 2 wt % of iron oxide, the mean prim~y particle size of said iron oxide being about 2~0 nm. These pa~ticles may also be ~oated with phospholipids.
It has become a generally accepted practi~e to specify the sun protection factor ~SP~) o~ ~un protection prep~a-tions. There is a great inte~est in increasin~ ~aid sun p~otection facto~ so that the product can be used by many people and in~ariably ca~ses a pleasant dermal se~sation.
The medl~m-~ange sun p~otection ~acto~s from SFP l~ to 20 are of pa~ticula~ interest in this respect.
It is the~efore the ob3ect of the invention ~o provide novel sun protection preparations having an improved ~un p~otection faotor.
2 0 A sun p~otection preparation a~co~ding to the in~ention ~onsists o~
(A) a fine-particle, crosslinked pol~methylsiloxane) with a particle s~ze ran~ing from 1 to 1~ ~m;
~B) ootyldodecy~ neopentanoa~e;
~C) formulation aids; and (D) addi~ives.
The rati~ of (A) to (~) ranges from 1 : 2 to 10, and the portion of (A) and (B) ranges f~om 3 to 12 wt %, relative to the total composition.
A p~ticularly ~dvantageous prepa~ation contains the componen~ (A) with a mean particle size of 4.5 ~m.
In another prefe~ed embodiment, the r~tio of (A) to ~3) ran~es f~o~ 1 : 2.5 to 8, prefe~ably ~rom 1 : 3 to 5.
In yet anothe~ prefe~red embodiment, the total portio~ of ~omponents (A) and (B) is 4 to ~ wt %, relati~e to the total ~omposition.
05~01~7 oa: 13 CA 02203 184 1997 04 18 1~1 004~013 The fine-pa~ticle, crosslinked poly(methylsiloxane) which constitu~es component (A) is a prod~c~ that speci~ically has t~e following properties:
- its weight los~ is 3~ or les~ a~ 35~ ~, and 12~ or less at 900 C;
- the pa~ticle diameter does ~ot chan~e when calcined in ai~
for ~our hours up to about 350 C and is reduced by 25~ or less at 9~ 'C while ~etaining its generally ~i~cular struc-tu~e;
- there are no endothe~mic pea~s when heated in air at a heating rate ~f 10 C per minute;
- it is ~esistant ~o organic solvents based on alcohols, ketones, es~ers, a~omates, and chlorinate~ hydrocarbons.
A particularl~ advantageous poly(methylsiloxane) is the comme~cial p~oduct named ~spea~l~, in particula~ Tospearl 1~5 by Toshiba Silic~ne Co., Ltd., avail~le f~om Kobo P~oducts, Inc., NJ, U.S A.
It is known tha~ component (~), octyldodecyl neopenta-n~ate (CTFA name), is an emollient. A partic~ ly advan-tageous comme~cial p~oduct is Elefac I Z05~ (available from Bermel chem. ~omp., Englewood, NJ, U.5.A.). When this c~mpo-nen~ (B) is used in a p~ep~ation with W screens and other c~mmon adjuvants and additives, a sun p~otection fsctor of about 16 is ~btained.
Su~p~isingly, the sun p~ection factor is in~rease~ up to about l~ o~ 1~ when adding small quantities o~
poly(methylsiloxane) as compo~ent (A~ Although it has been known that the crosslinked polyme~ (A) is highly heat-~esis-3~ tant, the~e was no information as to its influence on W
~adi~tion.
The components (A) a~d ~B) can be encapsula~ed in common liposomes.
In a particularly advantageous embodiment, components (A) 3S and ~B) aXe present in asy~et~ic lamellar agg~eg~tes con-sisting of phospholipids and ~luorocarbons charged ~i~h 05~0~/~7 oa 13 FAX ~13 230 8842CA 02203l84 l997-04-l8 1~loo5~ol3 oxygen or fluoroca~bon mixtures, the portion of fluoroca~bon ranging from ~.2 to 100~ w/v, the phosp~atidylcholine con-tent of the lipid f~action being f~om 30 to 9 g wt % r and comp~ising skin penetrati~n capability depending on the critical solubility temperatu~e o~ fluo~oca~bons (into n-hexane). The incorporation of the com~onents (A) and (B) in said novel asymmet~ic lamella~ aggregates known f~om W094/00098 may f~cilitate the particula~ly deep penetration of the components that act against UV radiation, which may contribute to improvin~ sun p~otection.
Unlike the known agueous liposomes ~vesicules), these hyd~ophobic phospholipid-~tabilized aggrega~es carry hydrophobic fluorocarbons in their core that are capable of transpo~ting oxygen. They are primarily stabilized at their interfacial ~ur~aces by an inversely arran~ed monolaye~ and, ~p~ionally, subsequent fo~ulation of bilayers. These novel aggregates are called asymmetric lame~lar oxygen car~iers because of their st~uctural peculiarities. The ext~aordinary ~olloidochemical st~bility of these aggre~ates is pr~ably 2~ due t~ their lamella~ structu~e and to their surface charge.
The latte~ is based cn selecting suitable phospholipids or natural or synthetic mixtu~es thereof. The substances ~eæponsible for an advanta~eous effect are, first of all, phospholipids, especially phosphatidylcholine at the spec-ified concentration of 30 to 99% combined with lysoleci~hins ha~ing a concentration of 0.1 to 10% and/or charged phospho-lipids with concentrations ranging from ~.1 to 30 wt %. The spe~ified effect of the phosp~olipids is verified by the respective negative zeta potentials and b~ charge density mea~uxements ~during tit~ation with a cationic polyelect~o-lyte). Penet~ation of the skin as a function of the ~ritical solubility tempe~ature of ~he fluorocarbons or fluo~ocarbon mixtu~es selected is essential fo~ the use of fluo~o~arbon aggregates (fox using aSymmetric lamellar agg~e~ates, see ~lso ~-B-42 21 2553.
05~01~7 0~:13 FAX ~13 230 884~cA 02203l84 1997-64-l8 1~00~013 The portion o~ aggregates cha~ged with sun-protective components may range f~om 5 to 60 ~t %, relative to the total preparation, preferably in the range from 10 to 50 wt %, most preferred f~om 30 to 5~ wt %.
As has been said above, common liposomes can be used as a transport sy6tem for the modified clay-containing mixture contained in the preparation of the invention. Lip~somes are totally enclosed lipid-bilaye~ ~embranes encompassing an aqueous vol~me. Liposomes can be unilamellar vesic~les (com-lU prising a single-membrane bilaye~) or multilamellar vesicules ~onionlike structures ~haracterized by multiple-membrane bila~ers, each of which being separated f~om the next by an aqueous layer). The bilayer consists of two lipid monolayers that have a hyd~ophobic tail section and a hydro-phili~ head section. The bilaye~s are str~ure~ in su~h a way that the h~drophobic (non-polar) t~ils of the lipid monolayers are oriented towards the centre of the bil~yer whereas their hyd~ophilic heads are oriented to~a~ds the a~ueous ph~se.
The production ~ liposomes from saturated or unsaturated lipids an~ their ~se as transpor~ systems have been desc~ibed in nu~erous patents. The modified clay-containing mixture can be worked in in a generally known way.
Other ingredients of the sun protection prepa~ation of the i~vention are additional W-B s~eens that may be oil-or wa~e~-soluble. These include, fo~ example, derivatives of aminoben~ic a~id, esters o~ cinnamic acid, esters of ~alicylic acid, benzophenone de~i~atives and s~lfonic acid de~ivati~es of benzophenone, sulfonic acid derivatives, sulfonic acid derivatives ~f 3-be~zyledene camphor, etc.
Fu~thermore, ino~ganic pigments such as oxides of ti~aniu~, zinc, i~on, circoni~ ilicium, m~nganese, al~inium, or mixtures thereof may be used. When including inorganic pig-ment~, however, i~ should be noted that their agglomeration has to be balanced ~y adding la~ger quantities of emulga-tors. In addition, so-called radical traps such as 05~0~7 0~ FA~ ~13 230 884?CA 02203184 l997 04-l8 1~loo7~ol3 - a-tocophe~o~ or tocopheryl acetate may be used. As the prod- u~ts of photochemical reactions freq~ently are ~adicals~
e.g. hyd~oxy radicals, hydroxyperoxy radicals, or superoxide ions and sin~let oxygen, other radical traps tha~ are suit-able for cosmetic prepa~ations may be used, e.g. trans-uro~anic acid.
The p~eparation of the invention further contains other adjuvants t~at are common in simil~r p~eparations. Thi~
includes stabilizers such ~s PE~-~, BHT (Protegol~), cross-linked alkyl acrylates (Pemulen~) as well as preser~atives such as phenoxy ethanol, parabens, ~ethyl dib~omoglutaro-nitrile, ~enzophenone-3, etc. and other gels and f~rances.
Mo~eove~, the preparation may ~on~ain plant extra~ts of a~oe vera and others.
~he sun protection preparation of the invention wi~h ~n increased sun p~otection factor is produ~ed using an emul-sification method in which the ~ng~edients are intermixed, optionally after separate emulsi~ication at increased te~-peratures. It is ad~antageous in this respect to add the component (A) immediately after the oil ph~se i~ the emulsification p~ocess. After bringing a~out s~ficient homogenization, the homogenate is rooled down to room tem-perature, and preservativefi and fragrances ~re added. It goes without saying that all processing has to take place under sterile conditions.
If the sun protection preparation contains the asymmetric lamellar aggregates ~entioned above, the components (A) and (B) a~e subsequently added to a perfluoroca~n while being p~ope~ly h~mogenized and, optionally, mixed with glycerine and p~opylene glycol/ and a phospholipid with a phosphati-dylcholine content of more than 3~ ad~ed under stirring to this homogenate. Subsequently, wate~ is added. After proper homogenizing, the aggregates ~ha~ged with light-pr~-tective components 2~e available for further intermingling 3~ with the suspension. If other li~ht-protective components are to be c~ntained in the finished preparation, these may 05~01~7 0~ FAX ~13 230 884~CA 02203184 l99q- 04- i8 [~1008~013 also be inte~mingled with said aggrega~es.
A particularly advantageous em~odiment o~ the sun p~otec-tion preparation acco~ding to the invention ~ay ~e an emul-sion or spray. If the preparation of the invention is formu-lated as a ~pray, it may be added with the typical known substances contained in a spray such as propellant~, especially non-polluting pr~pellants, so that the prod~t is ready fo~ use in an ae~o~ol spray can.
The inventi~n ~hall now be explained in greater detail lo based on examples. The percentages ~iven in ~hese examples are percentage~ by weight.
Example L
Phenyltrimethicone ~- %
~ocopheryl acetate 2.00 %
Octyldode~yl neopentanoate 4.00 %
~isabolol 5 %
I60stearyl neopentano~te 1.50 ~
~HT 0-07 %
Acrylate / ClQ-30 alkyl acrylate c~osspolyme~ 0.25 Benzop~enone-3 2.00 Octyl methoxycinnamate 7.50 ~
2-Phenylbenzimidazole-5-sulfonic acid 16.00 %
Panthenol ~ propylene glycol 3.00 Acrylates copolymer ~ melanin & PPG-2 myristyl ether pxopionate & methylpa~a~en p~opylpa~aben 0.20 Aloe vera gel 0.10 ~
Disodium EDTA o.05 %
PEG-8 5.00 %
Ca~bomer 0.20 %
Polymethylsilse~uioxane (Tospearl 145~) 1.00 %
Phenoxyethanol h (Methyl-e~hyl-propyl-butyl) paraben~ ~-5~ $
Met~yldibromo gluta~onitrile ~ phenoxyethan~l O.SO %
FragranCe $ %
Wate~ ad loo 05/0~7 0~:14 FAX ~13 230 884?CA 02203l84 l997-04-18 1~loo~ol3 The prepa~ation was produced as follows: an aqueo~s and an oil phase were emul~ified by homogeniz~ion at the usual temperatures in the ~ange from 50 to 75 C. The aqueous phase was added with disodium EDTA, PEG-8, aloe ~era, t~en polymethylsil~esquioxane, and finally the carbomer. A~ter ~he batch had turned into a dispersion and been heated to approx. 7~ '~, 2-phenylbenzimidazol-5-sulfonic acid was added.
The oil phase was p~o~uced by mixing phenyl t~imethicone, tocophe~yl acetate, oc~yldodecyl neopentanoate, bisabolol, iso~tearyl neopent~noate, and ~HT, and by preheating this mixture to ~O C. Octyl methoxycinnamate and benzophenone are simultaneously mixed and slightly heated, and added to the oil phase. Finally, acrylate / ~10-30 alkyl acryl~te crosspolyme~ is added while the ~ixture is prope~ly homog~n-ized until a dispe~sion of the oil phase i~ obtained.
After emul~ifying the oil and the aqueous phases and cooling to about 40 C, ac~ylates copolyme~ ~ melanin ~ PPG-2 myristyl ethe~ propionate & methylpa~a~en & p~opylpa~a~en and p~nthenol~p~opylene glycol is added followed b~ protec-tive agents and f ~ag~ance components.
Exa~.ple 2: Liposo~es A phospholipid with soluble animal collagen an~
hyd~oly~ed mucopoly-~accha~ide~ was placed in an aqueous suspension of polymethylsil~e~quioxane and octyldodecyl neopentanoate. A~ter proper homogenization, this suspension was added to the dispersion obtained in Example 1 containing the other ingredients, then homogenizing wa~ continued so that the por~ion of liposome~ was app~ox. 5 ~.
~xample 3: Aggregates A perflu~oca~bon (pe~fluorodec~line) mixed with glyce~in and p~opylene glycol was inte~mixe~ with polymethylsil-6esquioxane and oc~yldodecyl neopentanc~ate, and a phospholipid containing 40% of phosphatidylcholine was added to this mixture. The mixtu~e was prope~ly homogenized. ~he asymmet~ic lamellar aggregate~ that were formed in this 05~01~7 Oa:14 FAX ~13 230 884?CA 02203~84 ~997-04-18 1~1olo~ol3 .
proces~ were added to the dispersion containing the othe~
ing~edients of the formulatio~ in accordance with Example 1 so that the total portion of llposo~es w~s appr~x. 5 %.
Refexence example 1 The processing was performed as in Example 1 except that the fine-particle, crosslinked poly(methylsilox~ne) (~FTA
name~ polymethylsilsesquio~ane~ was not ~ontained and th~t the portion of octyldodecyl neopentanoate was only ~.00~.
~ixing was performed in a 6imila~ way as in Example 1. The sun protection factor obt~ined for the formulation was below 16.1~ (prior to immexsion) and below 15.~4 after immersion.
The sun protection facto~ of the formulation prep~red in accordance with Example 1 was ~9.Ho ~prior to im~ersion) and 17.00 after im~e~sion.
lS The sun pxotection factor wa~ measu~ed in acco~dance with a regulation issued ~y the U.S. Food and Drug Ad~in;~tration ~FDA) by exposing a group o~ ~ people treated with the sun protection prep~ration of the invention ~nd with the prep-~ation of the re~erence example to the 150 ~ xenon a~c lamp 2~ of a 1~ s sola~ ultra~iolet simul~tor.
~he results show that the sun pro~ection $acto~ could be signific~ntly increased by adding poly(methylsiloxane).
(A) a fine-particle, crosslinked pol~methylsiloxane) with a particle s~ze ran~ing from 1 to 1~ ~m;
~B) ootyldodecy~ neopentanoa~e;
~C) formulation aids; and (D) addi~ives.
The rati~ of (A) to (~) ranges from 1 : 2 to 10, and the portion of (A) and (B) ranges f~om 3 to 12 wt %, relative to the total composition.
A p~ticularly ~dvantageous prepa~ation contains the componen~ (A) with a mean particle size of 4.5 ~m.
In another prefe~ed embodiment, the r~tio of (A) to ~3) ran~es f~o~ 1 : 2.5 to 8, prefe~ably ~rom 1 : 3 to 5.
In yet anothe~ prefe~red embodiment, the total portio~ of ~omponents (A) and (B) is 4 to ~ wt %, relati~e to the total ~omposition.
05~01~7 oa: 13 CA 02203 184 1997 04 18 1~1 004~013 The fine-pa~ticle, crosslinked poly(methylsiloxane) which constitu~es component (A) is a prod~c~ that speci~ically has t~e following properties:
- its weight los~ is 3~ or les~ a~ 35~ ~, and 12~ or less at 900 C;
- the pa~ticle diameter does ~ot chan~e when calcined in ai~
for ~our hours up to about 350 C and is reduced by 25~ or less at 9~ 'C while ~etaining its generally ~i~cular struc-tu~e;
- there are no endothe~mic pea~s when heated in air at a heating rate ~f 10 C per minute;
- it is ~esistant ~o organic solvents based on alcohols, ketones, es~ers, a~omates, and chlorinate~ hydrocarbons.
A particularl~ advantageous poly(methylsiloxane) is the comme~cial p~oduct named ~spea~l~, in particula~ Tospearl 1~5 by Toshiba Silic~ne Co., Ltd., avail~le f~om Kobo P~oducts, Inc., NJ, U.S A.
It is known tha~ component (~), octyldodecyl neopenta-n~ate (CTFA name), is an emollient. A partic~ ly advan-tageous comme~cial p~oduct is Elefac I Z05~ (available from Bermel chem. ~omp., Englewood, NJ, U.5.A.). When this c~mpo-nen~ (B) is used in a p~ep~ation with W screens and other c~mmon adjuvants and additives, a sun p~otection fsctor of about 16 is ~btained.
Su~p~isingly, the sun p~ection factor is in~rease~ up to about l~ o~ 1~ when adding small quantities o~
poly(methylsiloxane) as compo~ent (A~ Although it has been known that the crosslinked polyme~ (A) is highly heat-~esis-3~ tant, the~e was no information as to its influence on W
~adi~tion.
The components (A) a~d ~B) can be encapsula~ed in common liposomes.
In a particularly advantageous embodiment, components (A) 3S and ~B) aXe present in asy~et~ic lamellar agg~eg~tes con-sisting of phospholipids and ~luorocarbons charged ~i~h 05~0~/~7 oa 13 FAX ~13 230 8842CA 02203l84 l997-04-l8 1~loo5~ol3 oxygen or fluoroca~bon mixtures, the portion of fluoroca~bon ranging from ~.2 to 100~ w/v, the phosp~atidylcholine con-tent of the lipid f~action being f~om 30 to 9 g wt % r and comp~ising skin penetrati~n capability depending on the critical solubility temperatu~e o~ fluo~oca~bons (into n-hexane). The incorporation of the com~onents (A) and (B) in said novel asymmet~ic lamella~ aggregates known f~om W094/00098 may f~cilitate the particula~ly deep penetration of the components that act against UV radiation, which may contribute to improvin~ sun p~otection.
Unlike the known agueous liposomes ~vesicules), these hyd~ophobic phospholipid-~tabilized aggrega~es carry hydrophobic fluorocarbons in their core that are capable of transpo~ting oxygen. They are primarily stabilized at their interfacial ~ur~aces by an inversely arran~ed monolaye~ and, ~p~ionally, subsequent fo~ulation of bilayers. These novel aggregates are called asymmetric lame~lar oxygen car~iers because of their st~uctural peculiarities. The ext~aordinary ~olloidochemical st~bility of these aggre~ates is pr~ably 2~ due t~ their lamella~ structu~e and to their surface charge.
The latte~ is based cn selecting suitable phospholipids or natural or synthetic mixtu~es thereof. The substances ~eæponsible for an advanta~eous effect are, first of all, phospholipids, especially phosphatidylcholine at the spec-ified concentration of 30 to 99% combined with lysoleci~hins ha~ing a concentration of 0.1 to 10% and/or charged phospho-lipids with concentrations ranging from ~.1 to 30 wt %. The spe~ified effect of the phosp~olipids is verified by the respective negative zeta potentials and b~ charge density mea~uxements ~during tit~ation with a cationic polyelect~o-lyte). Penet~ation of the skin as a function of the ~ritical solubility tempe~ature of ~he fluorocarbons or fluo~ocarbon mixtu~es selected is essential fo~ the use of fluo~o~arbon aggregates (fox using aSymmetric lamellar agg~e~ates, see ~lso ~-B-42 21 2553.
05~01~7 0~:13 FAX ~13 230 884~cA 02203l84 1997-64-l8 1~00~013 The portion o~ aggregates cha~ged with sun-protective components may range f~om 5 to 60 ~t %, relative to the total preparation, preferably in the range from 10 to 50 wt %, most preferred f~om 30 to 5~ wt %.
As has been said above, common liposomes can be used as a transport sy6tem for the modified clay-containing mixture contained in the preparation of the invention. Lip~somes are totally enclosed lipid-bilaye~ ~embranes encompassing an aqueous vol~me. Liposomes can be unilamellar vesic~les (com-lU prising a single-membrane bilaye~) or multilamellar vesicules ~onionlike structures ~haracterized by multiple-membrane bila~ers, each of which being separated f~om the next by an aqueous layer). The bilayer consists of two lipid monolayers that have a hyd~ophobic tail section and a hydro-phili~ head section. The bilaye~s are str~ure~ in su~h a way that the h~drophobic (non-polar) t~ils of the lipid monolayers are oriented towards the centre of the bil~yer whereas their hyd~ophilic heads are oriented to~a~ds the a~ueous ph~se.
The production ~ liposomes from saturated or unsaturated lipids an~ their ~se as transpor~ systems have been desc~ibed in nu~erous patents. The modified clay-containing mixture can be worked in in a generally known way.
Other ingredients of the sun protection prepa~ation of the i~vention are additional W-B s~eens that may be oil-or wa~e~-soluble. These include, fo~ example, derivatives of aminoben~ic a~id, esters o~ cinnamic acid, esters of ~alicylic acid, benzophenone de~i~atives and s~lfonic acid de~ivati~es of benzophenone, sulfonic acid derivatives, sulfonic acid derivatives ~f 3-be~zyledene camphor, etc.
Fu~thermore, ino~ganic pigments such as oxides of ti~aniu~, zinc, i~on, circoni~ ilicium, m~nganese, al~inium, or mixtures thereof may be used. When including inorganic pig-ment~, however, i~ should be noted that their agglomeration has to be balanced ~y adding la~ger quantities of emulga-tors. In addition, so-called radical traps such as 05~0~7 0~ FA~ ~13 230 884?CA 02203184 l997 04-l8 1~loo7~ol3 - a-tocophe~o~ or tocopheryl acetate may be used. As the prod- u~ts of photochemical reactions freq~ently are ~adicals~
e.g. hyd~oxy radicals, hydroxyperoxy radicals, or superoxide ions and sin~let oxygen, other radical traps tha~ are suit-able for cosmetic prepa~ations may be used, e.g. trans-uro~anic acid.
The p~eparation of the invention further contains other adjuvants t~at are common in simil~r p~eparations. Thi~
includes stabilizers such ~s PE~-~, BHT (Protegol~), cross-linked alkyl acrylates (Pemulen~) as well as preser~atives such as phenoxy ethanol, parabens, ~ethyl dib~omoglutaro-nitrile, ~enzophenone-3, etc. and other gels and f~rances.
Mo~eove~, the preparation may ~on~ain plant extra~ts of a~oe vera and others.
~he sun protection preparation of the invention wi~h ~n increased sun p~otection factor is produ~ed using an emul-sification method in which the ~ng~edients are intermixed, optionally after separate emulsi~ication at increased te~-peratures. It is ad~antageous in this respect to add the component (A) immediately after the oil ph~se i~ the emulsification p~ocess. After bringing a~out s~ficient homogenization, the homogenate is rooled down to room tem-perature, and preservativefi and fragrances ~re added. It goes without saying that all processing has to take place under sterile conditions.
If the sun protection preparation contains the asymmetric lamellar aggregates ~entioned above, the components (A) and (B) a~e subsequently added to a perfluoroca~n while being p~ope~ly h~mogenized and, optionally, mixed with glycerine and p~opylene glycol/ and a phospholipid with a phosphati-dylcholine content of more than 3~ ad~ed under stirring to this homogenate. Subsequently, wate~ is added. After proper homogenizing, the aggregates ~ha~ged with light-pr~-tective components 2~e available for further intermingling 3~ with the suspension. If other li~ht-protective components are to be c~ntained in the finished preparation, these may 05~01~7 0~ FAX ~13 230 884~CA 02203184 l99q- 04- i8 [~1008~013 also be inte~mingled with said aggrega~es.
A particularly advantageous em~odiment o~ the sun p~otec-tion preparation acco~ding to the invention ~ay ~e an emul-sion or spray. If the preparation of the invention is formu-lated as a ~pray, it may be added with the typical known substances contained in a spray such as propellant~, especially non-polluting pr~pellants, so that the prod~t is ready fo~ use in an ae~o~ol spray can.
The inventi~n ~hall now be explained in greater detail lo based on examples. The percentages ~iven in ~hese examples are percentage~ by weight.
Example L
Phenyltrimethicone ~- %
~ocopheryl acetate 2.00 %
Octyldode~yl neopentanoate 4.00 %
~isabolol 5 %
I60stearyl neopentano~te 1.50 ~
~HT 0-07 %
Acrylate / ClQ-30 alkyl acrylate c~osspolyme~ 0.25 Benzop~enone-3 2.00 Octyl methoxycinnamate 7.50 ~
2-Phenylbenzimidazole-5-sulfonic acid 16.00 %
Panthenol ~ propylene glycol 3.00 Acrylates copolymer ~ melanin & PPG-2 myristyl ether pxopionate & methylpa~a~en p~opylpa~aben 0.20 Aloe vera gel 0.10 ~
Disodium EDTA o.05 %
PEG-8 5.00 %
Ca~bomer 0.20 %
Polymethylsilse~uioxane (Tospearl 145~) 1.00 %
Phenoxyethanol h (Methyl-e~hyl-propyl-butyl) paraben~ ~-5~ $
Met~yldibromo gluta~onitrile ~ phenoxyethan~l O.SO %
FragranCe $ %
Wate~ ad loo 05/0~7 0~:14 FAX ~13 230 884?CA 02203l84 l997-04-18 1~loo~ol3 The prepa~ation was produced as follows: an aqueo~s and an oil phase were emul~ified by homogeniz~ion at the usual temperatures in the ~ange from 50 to 75 C. The aqueous phase was added with disodium EDTA, PEG-8, aloe ~era, t~en polymethylsil~esquioxane, and finally the carbomer. A~ter ~he batch had turned into a dispersion and been heated to approx. 7~ '~, 2-phenylbenzimidazol-5-sulfonic acid was added.
The oil phase was p~o~uced by mixing phenyl t~imethicone, tocophe~yl acetate, oc~yldodecyl neopentanoate, bisabolol, iso~tearyl neopent~noate, and ~HT, and by preheating this mixture to ~O C. Octyl methoxycinnamate and benzophenone are simultaneously mixed and slightly heated, and added to the oil phase. Finally, acrylate / ~10-30 alkyl acryl~te crosspolyme~ is added while the ~ixture is prope~ly homog~n-ized until a dispe~sion of the oil phase i~ obtained.
After emul~ifying the oil and the aqueous phases and cooling to about 40 C, ac~ylates copolyme~ ~ melanin ~ PPG-2 myristyl ethe~ propionate & methylpa~a~en & p~opylpa~a~en and p~nthenol~p~opylene glycol is added followed b~ protec-tive agents and f ~ag~ance components.
Exa~.ple 2: Liposo~es A phospholipid with soluble animal collagen an~
hyd~oly~ed mucopoly-~accha~ide~ was placed in an aqueous suspension of polymethylsil~e~quioxane and octyldodecyl neopentanoate. A~ter proper homogenization, this suspension was added to the dispersion obtained in Example 1 containing the other ingredients, then homogenizing wa~ continued so that the por~ion of liposome~ was app~ox. 5 ~.
~xample 3: Aggregates A perflu~oca~bon (pe~fluorodec~line) mixed with glyce~in and p~opylene glycol was inte~mixe~ with polymethylsil-6esquioxane and oc~yldodecyl neopentanc~ate, and a phospholipid containing 40% of phosphatidylcholine was added to this mixture. The mixtu~e was prope~ly homogenized. ~he asymmet~ic lamellar aggregate~ that were formed in this 05~01~7 Oa:14 FAX ~13 230 884?CA 02203~84 ~997-04-18 1~1olo~ol3 .
proces~ were added to the dispersion containing the othe~
ing~edients of the formulatio~ in accordance with Example 1 so that the total portion of llposo~es w~s appr~x. 5 %.
Refexence example 1 The processing was performed as in Example 1 except that the fine-particle, crosslinked poly(methylsilox~ne) (~FTA
name~ polymethylsilsesquio~ane~ was not ~ontained and th~t the portion of octyldodecyl neopentanoate was only ~.00~.
~ixing was performed in a 6imila~ way as in Example 1. The sun protection factor obt~ined for the formulation was below 16.1~ (prior to immexsion) and below 15.~4 after immersion.
The sun protection facto~ of the formulation prep~red in accordance with Example 1 was ~9.Ho ~prior to im~ersion) and 17.00 after im~e~sion.
lS The sun pxotection factor wa~ measu~ed in acco~dance with a regulation issued ~y the U.S. Food and Drug Ad~in;~tration ~FDA) by exposing a group o~ ~ people treated with the sun protection prep~ration of the invention ~nd with the prep-~ation of the re~erence example to the 150 ~ xenon a~c lamp 2~ of a 1~ s sola~ ultra~iolet simul~tor.
~he results show that the sun pro~ection $acto~ could be signific~ntly increased by adding poly(methylsiloxane).
Claims (7)
1. A sun protection preparation with an increased sun protection factor consisting of (A) a fine-particle, crosslinked poly(methylsiloxane) with a particle size ranging from 1 to 10 µm, and comprising the following parameters:
- its weight loss is 3% or less at 350 °C, and 12% or less at 900 °C;
- the particle diameter does not change when calcined in air for four hours up to about 350 °C and is reduced by 25% or less at 900 °C while retaining its generally circular structure;
- there is no endothermic peak when heated in air at a heating rate of 10 °C per minute;
- it is resistant to organic solvents based on alcohols, ketones, esters, aromates, and chlorinated hydrocarbons.
(B) octyldodecyl neopentanoate;
(C) formulation aids; and (D) additives;
besides common sun protection agents;
wherein the ratio of (A) to (B) ranges from 1 : 2 to 10, and the portion of (A) and (B) ranges from 3 to 12 wt %, relative to the total composition.
- its weight loss is 3% or less at 350 °C, and 12% or less at 900 °C;
- the particle diameter does not change when calcined in air for four hours up to about 350 °C and is reduced by 25% or less at 900 °C while retaining its generally circular structure;
- there is no endothermic peak when heated in air at a heating rate of 10 °C per minute;
- it is resistant to organic solvents based on alcohols, ketones, esters, aromates, and chlorinated hydrocarbons.
(B) octyldodecyl neopentanoate;
(C) formulation aids; and (D) additives;
besides common sun protection agents;
wherein the ratio of (A) to (B) ranges from 1 : 2 to 10, and the portion of (A) and (B) ranges from 3 to 12 wt %, relative to the total composition.
2. The sun protection preparation according to claim 1 wherein the mean particle size is 4.5 µm.
3. The sun protection preparation according to claim 1 wherein the ratio of (A) to (B) ranges from 1 : 2.5 to 8, and preferably is 1 : 5.
4. The sun protection preparation according to claim 1 wherein the portion of (A) and (B) ranges from 4 to 8 wt %, relative to the total composition.
5. The sun protection preparation according to claim 1 wherein the fine-particle, crosslinked poly(methylsiloxane) and component (B) are encapsulated in liposomes.
6. The sun protection preparation according to claim 1 wherein (A) and (B) are present in the form of asymmetric lamellar aggregates consisting of phospholipids and fluorocarbons or fluorocarbon mixtures charged with oxygen, the portion of fluorocarbons ranging from 0.2 to 100% w/v, and the phosphatidylcholine content of the lipid fraction being 30 to 90 wt %, and wherein the penetration of the skin by said aggregates is dependent upon the critical solubility temperature of the fluorocarbons.
7. The sun protection preparation according to claim l wherein the formulation is present in the form of a lotion or spray.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4443243.7 | 1994-11-24 | ||
| DE4443243A DE4443243C2 (en) | 1994-11-24 | 1994-11-24 | Sunscreen preparation with increased SPF |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2203184A1 true CA2203184A1 (en) | 1996-05-30 |
Family
ID=6534956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002203184A Abandoned CA2203184A1 (en) | 1994-11-24 | 1995-11-23 | Sun-protection preparation with increased light-protection factor |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5885558A (en) |
| EP (1) | EP0793480B1 (en) |
| AT (1) | ATE172107T1 (en) |
| AU (1) | AU692969B2 (en) |
| CA (1) | CA2203184A1 (en) |
| DE (2) | DE4443243C2 (en) |
| ES (1) | ES2125674T3 (en) |
| WO (1) | WO1996015772A2 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19735899A1 (en) * | 1997-08-19 | 1999-02-25 | Beiersdorf Ag | Active ingredient combinations of one or more surface-active substances and oligomeric or polymeric UV filter substances with periodically repeating Si-0 groups |
| US20030113357A1 (en) * | 2000-05-23 | 2003-06-19 | The Procter & Gamble Company | Skin Care Compositions |
| WO2002003925A1 (en) * | 2000-07-07 | 2002-01-17 | Collaborative Technologies, Inc. | Method for preparing topical preparations containing skin protective agents with enhanced barrier properties |
| US6663853B2 (en) * | 2000-11-30 | 2003-12-16 | Blistex Inc. | Lip care moisturizer |
| US20040026462A1 (en) * | 2002-08-12 | 2004-02-12 | Blue Magic, Inc. | Oxygenated air freshener |
| US20050249689A1 (en) * | 2004-05-10 | 2005-11-10 | An-Li Kuo | Personal care compositions with enhanced properties, method of manufacture, and method of use thereof |
| US7887785B2 (en) * | 2004-05-10 | 2011-02-15 | Momentive Performance Materials Inc. | Personal care compositions with enhanced properties, method of manufacture, and method of use thereof |
| US20060134537A1 (en) * | 2004-12-17 | 2006-06-22 | Lexmark International, Inc. | Increased silicon microspheres in charge transfer layers |
| FR2920984B1 (en) * | 2007-09-19 | 2010-03-26 | Oreal | COMPOSITION COMPRISING A CONTINUOUS FATTY PHASE AND A PARTICULAR ESTER |
| EP2353584B1 (en) * | 2009-06-01 | 2017-08-23 | L'Oréal | Cosmetic composition based on a block polymer and a non volatile ester oil |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1272136A (en) * | 1985-04-02 | 1990-07-31 | Grish Chandra | Substantive skin care compositions comprising a polydiorganosiloxane |
| CA2029045C (en) * | 1989-11-29 | 1995-02-07 | Lauren Ann Thaman | Photoprotection compositions having improved efficiency |
| WO1993011095A1 (en) * | 1991-11-27 | 1993-06-10 | Richardson-Vicks Inc. | Uva-absorbing sunscreen metal complexes |
| GB9126440D0 (en) * | 1991-12-12 | 1992-02-12 | Boots Co Plc | Sunscreen compositions |
| GB9203806D0 (en) * | 1992-02-21 | 1992-04-08 | Unilever Plc | Sunscreen agents |
| US5266307A (en) * | 1992-03-31 | 1993-11-30 | The Regents Of The University Of Michigan | Retinoic acid as a skin tanning agent in persons of light skin color |
| DE4221269C1 (en) * | 1992-06-26 | 1993-12-09 | Lancaster Group Ag | Preparation for topical use |
| MX9305746A (en) * | 1992-09-22 | 1994-05-31 | Colgate Palmolive Co | HAIR CONDITIONING SHAMPOO CONTAINING HIGH LOAD DENSITY POLYMERS. |
| ES2201075T3 (en) * | 1993-02-26 | 2004-03-16 | Estee Lauder Inc. | DISPERSIONS OF TITANIUM DIOXIDE, COSMETIC COMPOSITIONS AND METHODS OF USE. |
-
1994
- 1994-11-24 DE DE4443243A patent/DE4443243C2/en not_active Expired - Fee Related
-
1995
- 1995-11-23 ES ES95940119T patent/ES2125674T3/en not_active Expired - Lifetime
- 1995-11-23 DE DE59503948T patent/DE59503948D1/en not_active Expired - Fee Related
- 1995-11-23 US US08/836,005 patent/US5885558A/en not_active Expired - Fee Related
- 1995-11-23 CA CA002203184A patent/CA2203184A1/en not_active Abandoned
- 1995-11-23 AU AU41706/96A patent/AU692969B2/en not_active Ceased
- 1995-11-23 EP EP95940119A patent/EP0793480B1/en not_active Expired - Lifetime
- 1995-11-23 AT AT95940119T patent/ATE172107T1/en not_active IP Right Cessation
- 1995-11-23 WO PCT/DE1995/001701 patent/WO1996015772A2/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996015772A3 (en) | 1996-07-25 |
| US5885558A (en) | 1999-03-23 |
| DE59503948D1 (en) | 1998-11-19 |
| WO1996015772A2 (en) | 1996-05-30 |
| AU692969B2 (en) | 1998-06-18 |
| EP0793480B1 (en) | 1998-10-14 |
| ES2125674T3 (en) | 1999-03-01 |
| DE4443243A1 (en) | 1996-06-05 |
| AU4170696A (en) | 1996-06-17 |
| EP0793480A2 (en) | 1997-09-10 |
| ATE172107T1 (en) | 1998-10-15 |
| DE4443243C2 (en) | 1998-02-19 |
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